Hi, thanks for the huge compliment, I truly appreciate it :)
I wonder what is behind your question. Do you think there's something like a specific step, an incantation or a method to follow? To be honest: there's really no satisfying way to answer you question from that perspective. It just happened.
I had been fucking around long enough, obviously, and it was time to go for it. Courage is not something you can get from something else. The whole 'fun' is exactly that it has to come from you, because that is the most fundamental quality of courage. So I would say not to wait for a magic moment or a specific time where the coast seems clear. You just begin, you just open up, and you don't hold back.
For most people this process or journey starts when there aren't many alternatives left. That is the Hero's Journey aspect of it. On the other hand I could just as well tell you that life is living you and will kick you in the ass hard enough if it somehow has the idea that it's about time.
I have no idea of this answer is helpful, but it's honest and spontaneous. If ever you'd like some solid, professional and heartfelt guidance, you could contact me and talk about coaching.
Hope this sparks something in you!